ZipRecruiter

Log In

1

Windows Server Jobs in Chicago, IL (NOW HIRING)

IPsoft Inc.

Windows Administrator

Chicago, IL

$45 - $56.50/hr

Diagnose and remediate issues with Windows Server Infrastructure, and related roles and features, as well as other Microsoft and third-party Windows business infrastructure applications, while ...

blueStone

Server Administrator

Hoffman Estates, IL

The Server Administrator is responsible for the installation, configuration and maintenance of the organization's Windows Server operating systems and all related systems software. The Server ...

FIS

Windows Systems Administrator

Rosemont, IL

Microsoft Windows server / workstation certification * CompTia certification * Network + or Security + certification What we offer you * A multifaceted job with a high degree of responsibility and a ...

MMD Services, Inc

Sr. Server Engineer

Chicago, IL · On-site

Windows-only or Linux-only candidates will not be the right fit.*** What You''ll Do * Own a ... Windows Server (2016+), AD, Group Policy, and PowerShell on one side; RHEL/Ubuntu command-line work ...

3B Staffing LLC

Windows Engineer

Chicago, IL · On-site

The project is to remediate vulnerabilities identified for windows desktop and servers. Top skillsets needed: They will focus on mitigating all security vulnerabilities across our Windows ...

Kirkland & Ellis LLP.

Server Engineer II

Chicago, IL · On-site

$116K - $144K/yr

As a Server Engineer II, you'll play a key role on our global Server Operations team, supporting ... global Windows and Linux environments; manage hypervisors including VMware vSphere, Nutanix ...

next page

Showing results 1-20

All JobsWindows Server JobsWindows Server Jobs in Chicago, IL

Windows Server information

See Chicago, IL salary details

$92.3K

$111.2K

$128.4K

How much do windows server jobs pay per year?

As of Jul 27, 2026, the average yearly pay for windows server in Chicago, IL is $111,152.00, according to ZipRecruiter salary data. Most workers in this role earn between $101,500.00 and $120,600.00 per year, depending on experience, location, and employer.

What are the roles of a Windows server?

A Windows Server administrator manages and maintains Windows server environments, including configuring roles such as Active Directory, DNS, DHCP, file and print services, and virtualization with Hyper-V. They ensure server security, performance, and availability, often using tools like PowerShell and requiring certifications like MCSA or MCSE. These roles support network infrastructure and enterprise IT operations.

What are the key skills and qualifications needed to thrive in the Windows Server position, and why are they important?

To thrive as a Windows Server Administrator, you need a solid understanding of Windows Server operating systems, Active Directory, networking, and systems troubleshooting, often backed by a relevant degree or IT certifications. Familiarity with tools such as PowerShell, Hyper-V, and certifications like Microsoft Certified: Windows Server Fundamentals or MCSA are typically required. Strong problem-solving skills, effective communication, and the ability to work well under pressure are important soft skills for this role. These abilities are essential to ensure reliable system performance, rapid issue resolution, and successful collaboration within IT teams.

What is the highest paying waitress job?

The highest paying waitress jobs are typically in upscale restaurants, fine dining establishments, or luxury hotels, where tips are higher due to affluent clientele. Experienced waitstaff with strong customer service skills and knowledge of wine or specialty beverages can earn significantly more through tips, with some earning over $50,000 annually. Certifications in wine or mixology can also enhance earning potential in these roles.

What can I do with a Windows server?

A Windows Server administrator manages and maintains Windows Server environments, including configuring network services, managing user accounts, deploying applications, and ensuring security and system stability. They often use tools like Active Directory, PowerShell, and Server Manager to perform these tasks and may hold certifications such as MCSA or MCSE.

What are some typical day-to-day responsibilities of a Windows Server Administrator?

As a Windows Server Administrator, your daily tasks often include monitoring server performance, applying updates and patches, managing user accounts through Active Directory, and resolving system issues to minimize downtime. You may also be responsible for backup operations, security checks, and supporting end-users or other IT staff with server-related concerns. Collaboration is common, as you'll frequently work alongside network administrators, cybersecurity professionals, and support teams to ensure seamless IT operations. These responsibilities require a proactive approach to system management and strong attention to detail. Developing your skills in this role can open up opportunities for advancement into senior administration or network management positions.

What is a Windows Server job?

A Windows Server job involves managing, maintaining, and troubleshooting Microsoft's Windows Server operating systems in an IT environment. Professionals in this role configure servers, ensure security, handle updates, and support network infrastructure. They may also work with Active Directory, virtualization, and cloud integration to optimize system performance.

What is the salary of a Windows Administrator?

The salary of a Windows Administrator typically ranges from $60,000 to $100,000 annually, depending on experience, certifications, and location. Entry-level positions may start lower, while experienced professionals with advanced skills and certifications like Microsoft Certified: Windows Server can earn higher salaries.
What are the most commonly searched types of Windows Server jobs in Chicago, IL? The most popular types of Windows Server jobs in Chicago, IL are:
What are popular job titles related to Windows Server jobs in Chicago, IL? For Windows Server jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Windows Server jobs in Chicago, IL look for? The top searched job categories for Windows Server jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Windows Server jobs? Cities near Chicago, IL with the most Windows Server job openings:
Windows Server jobs near you
Infographic showing various Windows Server job openings in Chicago, IL as of July 2026, with employment types broken down into 73% Full Time, 23% Part Time, 1% Temporary, and 3% Contract. Highlights an 94% Physical, 2% Hybrid, and 4% Remote job distribution, with an average salary of $111,152 per year, or $53.4 per hour.

Windows Server Team Lead

CTC Lateral - Website & LinkedIn

Chicago, IL • Hybrid

Other

Posted 21 days ago

Job description

As a Windows Server Team Lead, you will work within Infrastructure to design, build, and operate scalable systems that support the business. Your focus will be on Windows server platforms, identity services, automation, and reliability engineering across onprem Windows environments and hybrid cloud integrations.

What You'll Do

  • Lead and develop a team of Windows Server engineers, setting priorities and focusing effort on highimpact reliability and platform initiatives.
  • Design and implement highperformance Windows Server solutions with a strong emphasis on availability, operational excellence, and latencysensitive trading workloads.
  • Drive automation and infrastructureascode practices to improve deployment consistency, reduce manual work, and scale operations.
  • Lead Active Directory modernization and hybrid identity initiatives, ensuring secure, reliable access across the firm.
  • Partner closely with Security, Infrastructure, and Development teams to plan and deliver changes safely and predictably.
  • Improve incident response through clear leadership during events, root cause analysis, and durable preventative followups.
  • Contribute to resource management, forecasting requirements, and enhancing performance to support peak market activity.
  • Produce and maintain documentation (runbooks, diagrams, postincident reviews) to support knowledge sharing and continuous improvement.
  • Participate in an oncall rotation and provide leadership during critical incidents as needed.

What We're Looking For

  • Good interpersonal skills with the ability to lead, mentor, and collaborate across technical teams.
  • A pragmatic approach that balances fast delivery with longterm maintainability and operational excellence.
  • Ability to triage and resolve issues endtoend, including clear ownership of root cause and prevention.
  • 8+ years of handson Windows Server administration experience in critical, highavailability environments.
  • Deep expertise in Windows Server, Active Directory, Group Policy, DNS, DHCP, and Failover Clustering, including performance tuning and resolving complex challenges.
  • Proven leadership experience running infrastructure teams (or acting as a senior technical lead), with a record of developing engineers and driving standards.
  • Strong PowerShell scripting/automation skills; experience with infrastructureascode tools and/or configuration management (or demonstrated willingness to adopt and lead these efforts).
  • Willingness to participate in an oncall rotation and lead through highseverity incidents.
  • Meticulous attention to procedure, change management, and meeting service expectations.

Nice to Haves

  • Experience with enterprise platforms such as SCCM/MECM, endpoint/server monitoring, backup systems, and/or load balancers.
  • Familiarity with ITIL concepts, operational workflows, project management, and DevOps/CI/CD practices.
  • Experience supporting financial services infrastructure, trading systems, or market data platforms.
  • Exposure to modern deployment approaches (e.g., containerization, orchestration).

Work Location and Collaboration

This role is based in Chicago, working closely with Infrastructure, Security, Networking, and Development teams for highbandwidth collaboration. We value facetoface teamwork and pragmatic flexibility.

Apply